Longest serving Chelsea managers of all-time!
Longest serving Chelsea managers of all-time? Which Chelsea managers have lasted the longest? Chelsea FC football managers? Jose Mourinho? Antonio Conte? Carlo Ancelotti? Who are The longest-lasting Chelsea managers?Â
Here we look at the longest serving Chelsea managers of all-time. We will look throughout history of Chelsea FC past managers to find out who were the best.
When you think of long-serving Chelsea FC football managers, Jose Mourinho probably comes to mind (depending on your age). But you’ll be surprised to find out that Jose Mourinho doesn’t even reach the Top 5 longest serving Chelsea managers.
Being a manager is tough these days. The managerial turn-over is very high. Its not uncommon to see a manager get sacked after just a few bad results. Watch & Bet Football Here =>
But back in the old days, Chelsea managers tended to last a lot longer. Perhaps it was a different time back then, or perhaps it’s because the current owner Roman Abramovich is very demanding.
Expectations are higher for Chelsea managers these days and the stakes are high. Managers such as Jose Mourinho and Carlo Ancelotti have been sacked for one bad season. Those two are probably two of the top five managers in the world.
So we could safely say that managers back in the old days before Roman Abramovich took over lasted a lot longer. But, you can’t fault the Russian billionaire. Clearly it works. Chelsea have won dozens of top trophies since 2003. Before then, Chelsea hadn’t won the top league in 50 years!
Longest serving Chelsea managers of all-time
So here we will list all Chelsea FC previous managers. In our Chelsea FC managers list, we will sort the managers from longest time at the club down to the shortest.
Longest serving all former Chelsea managers list
So finally, here are the longest-serving Chelsea managers of all-time. Watch & Bet Football Here =>
| Chelsea FC Manager | From | To | Games |
| David Calderhead | 01/08/07 | 08/05/33 | 966 |
| Ted Drake | 01/06/52 | 30/09/61 | 426 |
| Dave Sexton | 23/10/67 | 03/10/74 | 371 |
| Tommy Docherty | 01/10/61 | 06/10/67 | 303 |
| Billy Birrell | 19/04/39 | 31/05/52 | 293 |
| Leslie Knighton | 08/05/33 | 19/04/39 | 269 |
| John Neal | 28/05/81 | 11/06/85 | 203 |
| Claudio Ranieri | 17/09/00 | 31/05/04 | 199 |
| José Mourinho | 02/06/04 | 19/09/07 | 185 |
| Bobby Campbell | 06/03/88 | 12/05/91 | 165 |
| Glenn Hoddle | 04/06/93 | 10/05/96 | 157 |
| John Hollins | 11/06/85 | 06/03/88 | 145 |
| Gianluca Vialli | 12/02/98 | 12/09/00 | 143 |
| José Mourinho | 03/06/13 | 17/12/15 | 136 |
| Carlo Ancelotti | 01/06/09 | 22/05/11 | 109 |
| Antonio Conte | 03/07/16 | 25/06/18 | 106 |
| Thomas Tuchel | 26/01/21 | 07/09/22 | 100 |
| Eddie McCreadie | 16/04/75 | 01/07/77 | 97 |
| Frank Lampard | 16/06/19 | 25/01/21 | 95 |
| Ian Porterfield | 11/06/91 | 15/02/93 | 90 |
| Ruud Gullit | 10/05/96 | 12/02/98 | 83 |
| Geoff Hurst | 13/09/79 | 23/04/81 | 81 |
| Ken Shellito | 07/07/77 | 13/12/78 | 66 |
| Maurizio Sarri | 30/06/2018 | 16/06/2019 | 63 |
| Avram Grant | 20/09/07 | 24/05/08 | 54 |
| John Tait Robertson | 01/08/05 | 27/11/06 | 54 |
| Mauricio Pochettino | 01/07/23 | 21/05/24 | 51 |
| Rafael BenÃtez | 21/11/12 | 27/05/13 | 48 |
| Roberto Di Matteo | 04/03/12 | 21/11/12 | 42 |
| André Villas-Boas | 22/06/11 | 04/03/12 | 40 |
| Luiz Felipe Scolari | 01/07/08 | 09/02/09 | 36 |
| Ron Suart | 03/10/74 | 16/04/75 | 34 |
| Danny Blanchflower | 14/12/78 | 11/09/79 | 32 |
| Graham Potter | 08/09/22 | 02/04/23 | 31 |
| Guus Hiddink | 19/12/15 | 16/05/16 | 27 |
| William Lewis | 27/11/06 | 01/08/07 | 27 |
| Guus Hiddink | 16/02/09 | 30/05/09 | 22 |
| David Webb | 15/02/93 | 11/05/93 | 13 |
| Bobby Gould | 23/04/81 | 01/05/81 | 2 |
| Graham Rix Ray Wilkins | 13/09/00 | 17/09/00 | 2 |
| Ron Suart | 06/10/67 | 23/10/67 | 2 |
| Ray Wilkins | 09/02/09 | 15/02/09 | 1 |
| Steve Holland | 17/12/15 | 19/12/15 | 1 |
| Bruno Saltor | 02/04/23 | 06/04/23 | 1 |
Number one longest-serving Chelsea manager of all-time: David Calderhead
David Calderhead is the longest serving Chelsea manager ever. The Scotsman was in charge of Chelsea from 1907 to 1933! That’s 26 years. That’s 966 games!
Calderhead was the first ever manager at Chelsea. Despite competing in a few cup finals, he never managed to win any silverware. Sadly, Calderhead died five years after he left Chelsea at the age of 73.
Second longest-serving Chelsea manager of all-time: Ted Drake
Ted Drake was the second longest-serving Chelsea manager. The Englishman was in charge at Chelsea from 1952 to 1961. Drake managed 426 games. He won 156 of them with a win percentage of 37%.
Third longest serving Chelsea manager: Dave Sexton
Dave Sexton is the third longest-serving manager of all-time. Sexton managed Chelsea from 1967 to 1974. That’s 371 games as manager of Chelsea. Watch & Bet Football Here =>
Who was Chelsea’s longest-serving manager?
Chelsea’s longest-serving manager of all time was David Calderhead, who managed the club from August 1, 1907, to May 8, 1933. His tenure lasted an incredible 26 years, during which he oversaw 966 games.
Despite his longevity, he never won a major trophy with Chelsea, although he did lead them to their first-ever FA Cup final in 1915 and helped secure their promotion to the First Division in 1912. His reign remains unmatched in Chelsea’s history.
Who was the longest-serving manager?
Once again, the longest-serving manager in Chelsea’s history is David Calderhead. No other manager has come close to his 26-year tenure. His time at the club spanned both World War I and the early professionalization of football.
While modern Chelsea managers rarely last more than a few years due to high expectations, Calderhead’s reign stands as a testament to an era when long-term stability was more common in football.
Who is the best manager in Chelsea history?
Determining Chelsea’s best manager depends on the criteria used—whether it’s trophies, impact, or playing style.
Jose Mourinho is widely considered the most influential, having won three Premier League titles (2004-05, 2005-06, 2014-15) along with multiple domestic cups. His ability to build dominant teams and his charismatic personality made him a fan favorite as “Choosen one”.
Thomas Tuchel made a massive impact in a short period by guiding Chelsea to their second UEFA Champions League title in 2021, reinforcing the club’s status as a European powerhouse.
Carlo Ancelotti led Chelsea to a historic Premier League and FA Cup double in 2009-10, playing some of the most attacking football in the club’s history.
Other notable managers include Antonio Conte, who won the Premier League in his first season (2016-17) with a record-breaking 30 wins, and Roberto Di Matteo, who delivered Chelsea’s first-ever Champions League trophy in 2012.
How many managers has Chelsea had in the last 15 years?
Chelsea is known for its high managerial turnover, especially under the ownership of Roman Abramovich and Todd Boehly.
In the last 15 years (2009-2024), the club has had 15 different managers, including interim and caretaker appointments:
Carlo Ancelotti (2009–2011) – Won the Premier League and FA Cup double in 2010
André Villas-Boas (2011–2012) – Sacked before finishing his first season
Roberto Di Matteo (2012) – Led Chelsea to their first-ever Champions League title
Rafael BenÃtez (2012–2013) – Won the Europa League
José Mourinho (2013–2015) – Won the Premier League in 2015
Guus Hiddink (2015–2016) – Came in as an interim manager
Antonio Conte (2016–2018) – Won the Premier League in his debut season
Maurizio Sarri (2018–2019) – Won the Europa League in 2019
Frank Lampard (2019–2021) – Managed a young Chelsea squad under a transfer ban
Thomas Tuchel (2021–2022) – Won the Champions League in 2021
Graham Potter (2022–2023) – Struggled before being sacked
Bruno Saltor (Interim, 2023) – Managed just one game
Frank Lampard (Interim, 2023) – Returned but struggled
Mauricio Pochettino (2023–2024) – A disappointing spell, failing to bring stability
Enzo Maresca (2024-Present)
Chelsea FC former managers that won titles list.
All ex Chelsea managers with honours list. All the Chelsea managers that have won titles list. This includes Chelsea managers since 2000.
Previous Chelsea Managers with honours list
| Name | Nat | Tenure | Honours |
|---|---|---|---|
| Ted Drake |  Â England |
1952–1961 | 1955 First Division 1955 FA Charity Shield |
| Tommy Docherty |  Â Scotland |
1961–1967 | 1965 Football League Cup |
| Dave Sexton | Â England |
1967–1974 | 1970 FA Cup 1971 European Cup Winners’ Cup |
| John Neal | Â England |
1981–1985 | 1984 Second Division |
| John Hollins | Â England |
1985–1988 | 1986 Full Members Cup |
| Bobby Campbell | Â England |
1988–1991 | 1989 Second Division 1990 Full Members Cup |
| Ruud Gullit |  Â Netherlands |
1996–1998 | 1997 FA Cup |
| Gianluca Vialli |  Â Italy |
1998–2000 | 1998 Football League Cup 1998 UEFA Cup Winners’ Cup 1998 UEFA Super Cup 2000 FA Cup 2000 FA Charity Shield |
| José Mourinho |   Portugal |
2004–2007 2013–2015 |
2005 Football League Cup 2005 Premier League 2005 FA Community Shield 2006 Premier League 2007 Football League Cup 2007 FA Cup 2015 Football League Cup 2015 Premier League |
| Guus Hiddink | Â Netherlands |
2009 2015–2016 |
2009 FA Cup |
| Carlo Ancelotti | Â Italy |
2009–2011 | 2009 FA Community Shield 2010 Premier League 2010 FA Cup |
| Roberto Di Matteo | Â Italy |
2012 | 2012 FA Cup 2012 UEFA Champions League |
| Rafael BenÃtez |  Â Spain |
2012–2013 | 2013 UEFA Europa League |
| Antonio Conte | Â Italy |
2016–208 | 2017 Premier League
2018 FA Cup |
See also:Â
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